WO1990014011A1 - Agent antifouling sous-marin - Google Patents

Agent antifouling sous-marin Download PDF

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Publication number
WO1990014011A1
WO1990014011A1 PCT/JP1990/000641 JP9000641W WO9014011A1 WO 1990014011 A1 WO1990014011 A1 WO 1990014011A1 JP 9000641 W JP9000641 W JP 9000641W WO 9014011 A1 WO9014011 A1 WO 9014011A1
Authority
WO
WIPO (PCT)
Prior art keywords
antifouling agent
antifouling
component
undersea
agent
Prior art date
Application number
PCT/JP1990/000641
Other languages
English (en)
Japanese (ja)
Inventor
Osamu Kadota
Kouichiroh Tsurumi
Makoto Ishimoto
Yoshihiro Honda
Original Assignee
Nippon Oil And Fats Co., Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nippon Oil And Fats Co., Ltd. filed Critical Nippon Oil And Fats Co., Ltd.
Priority to EP90907465A priority Critical patent/EP0425709B1/fr
Priority to JP2507431A priority patent/JP2910241B2/ja
Publication of WO1990014011A1 publication Critical patent/WO1990014011A1/fr
Priority to NO910193A priority patent/NO179121C/no

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • A01N47/14—Di-thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/16—Antifouling paints; Underwater paints
    • C09D5/1606—Antifouling paints; Underwater paints characterised by the anti-fouling agent
    • C09D5/1612—Non-macromolecular compounds
    • C09D5/1625—Non-macromolecular compounds organic
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/74—Synthetic polymeric materials
    • A61K31/745—Polymers of hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/16—Antifouling paints; Underwater paints
    • C09D5/1687—Use of special additives

Definitions

  • the present invention relates to a novel marine antifouling agent for treating a fibrous or rope-like material to be inundated.
  • marine antifouling agents containing an organic tin compound such as TBT (tributyltin compound) as an active ingredient have been widely used. Suspicion of the accumulation of active ingredients has led to widespread use of self-control.
  • these organotin compounds are used as antifouling agents a) Japanese Patent Publication No. 62-439692 discloses a technique using a dialkylpolysulfide compound as an active ingredient, and b) Japanese Patent Application Laid-Open No. 60-38306 discloses a tetramer. Disclosed are technologies relating to antifouling agents for fishing nets having alkylthiuram disulfide, dialkyl polysulfide, and 2- (thiocyanomethylthio) benzothiazole as active ingredients, respectively.
  • JP-A-1-178562 a copolymer having specific hydrophilicity and a thiocyanoalkylthiopentazoheterozole.
  • An object of the present invention is to provide a marine antifouling agent capable of controlling the elution rate of an antifouling agent from a fibrous or rope-like material to be immersed over a long period of time and necessary and sufficiently. are doing. Disclosure of the invention
  • the present inventors have conducted intensive studies to achieve the above-mentioned object.
  • a submarine antifouling agent that can be controlled at a minimum was found, and the present invention was completed.
  • the present invention provides the following components A to C;
  • a 1 2 — (thiocyanomethylthio) benzothiazole, A 2: tetraethylthiuram disulphide,
  • R, and R 2 are each an alkyl group having 1 to 20 carbon atoms, and n is an integer of 1 to 5)
  • the present invention relates to the second invention relating to a marine antifouling treatment agent that additionally contains water.
  • Component A which is the antifouling agent of the marine antifouling agent of the present invention, is 2- (thiocyanomethylthio) benzothiazole, tetraethylthiuramum disulfide, 2,4,5,6-tetrat 1,2-Dicyanobenzene, N— (Ethylmethylphenyl) -dichloromethane Reid, N— (Jethylfenyl) One of dichloroaminoreid, at least one of Yes, all of these agents are known as low-toxic antifouling agents.
  • the component used as a film forming agent in the marine antifouling agent of the present invention includes, for example, natural resins for general coatings, rosins, modified rosins, fatty acids and oil-based varnishes conventionally used, synthetic rubbers, chlorinated rubbers, polychlorinated rubber, and polystyrene. And butadiene copolymers and acrylic resins. Further, an acrylic hydrophilic polymer synthesized using a specific hydrophilic monomer as shown in the production examples described later is preferably used.
  • Component C used as a dissolution controlling agent of the marine antifouling agent of the present invention has the following general formula (1):
  • R, and R 2 are each an alkyl group having 1 to 20 carbon atoms, and n is an integer of 1 to 5)
  • component D which is another dissolution controlling agent used only in the marine antifouling agent of the second invention of the present application, is a polybutene having a degree of polymerization of 2 to 100, which is generally a resin softening agent.
  • Specific examples thereof include various types of Nissan polybutene (polybis), such as polybutene 06 N and polybutene 15 N (manufactured by NOF Corporation).
  • Component A occupies 0.3 to 60% by weight of component A, preferably 0.5 to 50% by weight. %, Component B is 3 to 60% by weight, preferably 5 to 30% by weight, component C is 1 to 30% by weight, preferably 2 to 25% by weight, and further component D in the treating agent of the second invention. Is 1 to 30% by weight, preferably 2 to 25% by weight.
  • the amount of component A is less than the above, the antifouling property is insufficient, and if it is too large, formation of a coating film becomes difficult.
  • the amount of the component B is small, it is difficult to form a coating film, and when the amount is too large, the antifouling property is insufficient and the dissolution control function is deteriorated.
  • the amount of the component C is small, the dissolution control function is deteriorated. If the amount of component D is too large, the elution control function is reduced, and it is difficult to form a coating film.
  • an organic solvent in addition to the components A to D, an organic solvent, another antifouling agent, a coloring agent, a thixotropic agent, an antifoaming agent, a thickener, a plasticizer, etc.
  • Various additives can be added as needed.
  • Organic solvents include, for example, toluene, xylene, and solvent Husa, pseudodocument, acetate, methylethylketone, methylisobutylketone, ethylacetate, butylacetate, ethylcellosolve, butylcellosolve, etc. can be used alone or as a mixture of two or more. Can be.
  • N_t butyl-N′—cyclopropyl-6— (methylthio) 1-1,3,5 — Triazines 1, 2, 4 — diamin, 3 — (3: 4-phenyl phenyl) 1-1, 1 dimethyl urea, N> N— dimethylamine N ′ — phenyl N '— (Funolelo di Gioro Mecchirecho) Sulfa Amid, N, N — Dimethyl i N' — Tril I N '-(Funorelo Gyro Rome Chilere) Sulfa Amid, N — (Fluorochloromethylthio) phthalimid, cuprous oxide, organotin compounds, zinc dimethyldithiocarbamate, dimethylethylthiocarbamate, and the like can be added to the extent that the effects of the present invention are not impaired.
  • N_t butyl-N′—cyclopropyl-6— (methylthio) 1-1,3,5
  • the sea proof Kitanasho Rizai consisting components a to C or components a to D, usually
  • the components above are adjusted by the possible to dissolve in an organic solvent with di resolver first class.
  • the adjusted underwater treatment agent will be immersed in a method suitable for each target material.
  • the entire composition was put into a beaker and dissolved by stirring with a dissolver to prepare the respective treating agents of Examples and Comparative Examples.
  • a 20 cm wide, 40 ⁇ length cut piece of a polyethylene knotless fish-spring (32 pieces, section 6) is immersed in the marine antifouling agents of the above Examples and Comparative Examples, and then immersed in the sea. Air dried for 48 hours. The fish net impregnated with the treatment agent was drowned 1.5 m below the surface of water in Aioi Port, Hyogo Prefecture, and the status of fouling by marine organisms was investigated for 6 months. The results of the antifouling test were evaluated on the following five levels.
  • Biofouling is less than 5% of net area.
  • Biofouling is less than 15% and more than 5% of net area.
  • the biofouling is less than 50% and 15% or more of the net area.
  • Biofouling is more than 50% of net area.
  • the same fish net as that used in the antifouling test was soaked with the treating agent in the same manner, and the same inundation was performed. After 6 months, the treated fish net was pulled up and immersed in a beaker containing 1 liter of seawater for 1 hour to elute the antifouling agent. Seawater eluted with the antifouling agent is analyzed by liquid chromatography to measure the elution amount of the antifouling agent did. The elution amount was expressed as the concentration (ppm) of anti-elution agent in 1 liter of seawater.
  • Examples 11 to 13 which are the marine antifouling treatment agents of the first invention of the present application, though slightly inferior to the second invention, the marine organisms in the antifouling test over a long period of 6 power months were examined. Adhesion was slight, and the elution amount of the antifouling agent after 6 months remained at 0.07 ppm.
  • the component C and the component D are simultaneously added to the marine antifouling agent of the present invention.
  • the dissolution rate of the drug As a result of proper control of the dissolution rate of the drug, its antifouling effect can be maintained for a long time, which has not been possible before.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Plant Pathology (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Paints Or Removers (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Agent anti-fouling sous-marin appliqué par imprégnation afin d'empêcher le dépôt à long terme d'organismes aquatiques, par exemple sur les filets de culture, sur les filets stationnaires de pêche, etc., et sur les éléments de support des filets, tels que les cordages; cet agent s'applique également sur des filets empêchant les méduses d'envahir les conduites d'admission d'eau de mer servant au refroidissement, ainsi que sur des matériaux servant à la protection de la côte. La première invention se rapporte à un agent antifouling sous-marin comprenant (A) au moins un composé sélectionné parmi (A1) 2-(thiocyanomethylthis)benzothiazole, (A2) disulfure de tétraéthylthiurame, (A3)2,4,5,6-tétrachloro-1,3-dicyanobenzène, (A4) N-(éthylméthylphényl)dichloromaléimide et (A5) N-(diéthylphényl)dichloromaléimide; (B) une substance filmogène, et (C) au moins un composé sélectionné parmi les polysulfures de dialkyle représentés par la formule générale R1-(S)n-R2. La deuxième invention se rapporte à un autre agent antifouling sous-marin comprenant en plus le composant suivant: (D) polybutène avec un degré de polymérisation compris entre 2 et 100, outre les composants (A) et (C) susmentionnés. L'incorporation du composant (C) ainsi que du composant (D) dans l'agent antifouling permet de réguler de manière appropriée la vitesse de libération du composant (A) constituant l'ingrédient actif de l'agent antifouling, de sorte que l'effet antifouling peut être maintenu pendant longtemps.
PCT/JP1990/000641 1989-05-19 1990-05-19 Agent antifouling sous-marin WO1990014011A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP90907465A EP0425709B1 (fr) 1989-05-19 1990-05-19 Agent antifouling sous-marin
JP2507431A JP2910241B2 (ja) 1989-05-19 1990-05-19 海中防汚処理剤
NO910193A NO179121C (no) 1989-05-19 1991-01-17 Undersjöisk grohemmende blanding

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP12643689 1989-05-19
JP1/126436 1989-05-19
JP2/107100 1990-04-23
JP10710090 1990-04-23

Publications (1)

Publication Number Publication Date
WO1990014011A1 true WO1990014011A1 (fr) 1990-11-29

Family

ID=26447168

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1990/000641 WO1990014011A1 (fr) 1989-05-19 1990-05-19 Agent antifouling sous-marin

Country Status (7)

Country Link
US (1) US5229436A (fr)
EP (1) EP0425709B1 (fr)
KR (1) KR0163053B1 (fr)
AU (1) AU624956B2 (fr)
CA (1) CA2033206C (fr)
NO (1) NO179121C (fr)
WO (1) WO1990014011A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6235340B1 (en) 1998-04-10 2001-05-22 Massachusetts Institute Of Technology Biopolymer-resistant coatings

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060002234A1 (en) * 2004-06-30 2006-01-05 Lobe Henry J Anti-biofouling seismic streamer casing and method of manufacture
DE102005011990A1 (de) * 2005-03-14 2006-09-21 Basf Ag Foulingresistente Polyurethane, insbesondere für maritime Anwendungen
EP4175473A1 (fr) 2020-07-01 2023-05-10 Laboratorios Miret, S.A. Tcmtb microencapsulé

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5634604A (en) * 1979-08-29 1981-04-06 Yoshitomi Pharmaceut Ind Ltd Antifouling agent
JPS56118006A (en) * 1980-02-23 1981-09-16 Yoshitomi Pharmaceut Ind Ltd Antifouling solution for fish net
JPS5818304A (ja) * 1981-07-27 1983-02-02 Mitsui Toatsu Chem Inc 漁網用防汚剤

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB573079A (en) * 1942-10-07 1945-11-06 Louis Arnold Jordan Improvements in and relating to paint and like compositions
JPS6017764B2 (ja) * 1976-07-10 1985-05-07 イハラケミカル工業株式会社 水中生物忌避剤
US4608433A (en) * 1982-01-18 1986-08-26 The Dow Chemical Company Inert monovalent hydrocarbon terminated polysulfide polymers
JPS59176201A (ja) * 1983-03-28 1984-10-05 Mitsui Toatsu Chem Inc 漁網用防汚剤
JPS6038306A (ja) * 1983-08-11 1985-02-27 Nippon Soda Co Ltd 漁網用防汚剤
JPH01110574A (ja) * 1987-10-26 1989-04-27 K I Kasei Kk 海中生物防汚塗料

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5634604A (en) * 1979-08-29 1981-04-06 Yoshitomi Pharmaceut Ind Ltd Antifouling agent
JPS56118006A (en) * 1980-02-23 1981-09-16 Yoshitomi Pharmaceut Ind Ltd Antifouling solution for fish net
JPS5818304A (ja) * 1981-07-27 1983-02-02 Mitsui Toatsu Chem Inc 漁網用防汚剤

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP0425709A4 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6235340B1 (en) 1998-04-10 2001-05-22 Massachusetts Institute Of Technology Biopolymer-resistant coatings

Also Published As

Publication number Publication date
US5229436A (en) 1993-07-20
AU624956B2 (en) 1992-06-25
CA2033206C (fr) 1997-10-07
AU5650990A (en) 1990-12-18
NO179121C (no) 1996-08-14
NO910193D0 (no) 1991-01-17
NO910193L (no) 1991-01-17
KR920700539A (ko) 1992-08-10
CA2033206A1 (fr) 1990-11-20
EP0425709B1 (fr) 1997-08-13
EP0425709A1 (fr) 1991-05-08
NO179121B (no) 1996-05-06
EP0425709A4 (en) 1992-08-19
KR0163053B1 (en) 1998-11-16

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